Aldol reaction of iododifluoroacetate-Zn and 2,2-difluoroketene silyl acetal

Osamu Kitagawa, Takeo Taguchi, Yoshiro Kobayashi

Research output: Contribution to journalArticle

111 Citations (Scopus)

Abstract

Generation of the Reformatsky reagent of difluoracetate from the iodide (2) and the difluoroketene silyl acetal (3), and their aldol reaction are described. High anti-selectivity with chiral aldehyde (5d, 5f) was found in the case of the ketene silyl acetal (3b). 2,2-Difluoro-2-deoxy analogs of D-ribo- and L-galactopyranosides (1a, 1b) were effectively prepared.

Original languageEnglish
Pages (from-to)1803-1806
Number of pages4
JournalTetrahedron Letters
Volume29
Issue number15
DOIs
Publication statusPublished - 1988
Externally publishedYes

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Acetals
Iodides
Galactose
Aldehydes
3-hydroxybutanal
ketene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Aldol reaction of iododifluoroacetate-Zn and 2,2-difluoroketene silyl acetal. / Kitagawa, Osamu; Taguchi, Takeo; Kobayashi, Yoshiro.

In: Tetrahedron Letters, Vol. 29, No. 15, 1988, p. 1803-1806.

Research output: Contribution to journalArticle

Kitagawa, Osamu ; Taguchi, Takeo ; Kobayashi, Yoshiro. / Aldol reaction of iododifluoroacetate-Zn and 2,2-difluoroketene silyl acetal. In: Tetrahedron Letters. 1988 ; Vol. 29, No. 15. pp. 1803-1806.
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